6-(1-fluoroethyl)-5-iodo-4-aminopyrimidine compounds process for preparation of the same and pest controllers for agricultural and horticultural use

ABSTRACT

The present invention relates to a 6-(1-fluoroethyl)-5-iodo-4-aminopyrimidine compound represented by the following formula (1): 
                 
         wherein Ar represents a phenyl group, a naphthyl group, a thienyl group, an indanyl group or a 1,4-benzodioxan-6-yl group, which is unsubstituted or substituted by 1 to 3 substituents selected from the group consisting of a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a haloalkoxy group having 1 to 4 carbon atoms and a phenoxy group; R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; *1 represents an asymmetric carbon atom; *2 represents an asymmetric carbon atom when R represents an alkyl group having 1 to 4 carbon atoms,
 
a process for preparing the same, and agricultural and horticultural chemicals for controlling noxious organisms.

This application is the national phase under 35 U.S. §371 of PCTInternational Application No. PCT/JP02/00064 which has an Internationalfiling date of Jan. 10, 2002, which designates the United States ofAmerica.

TECHNICAL FIELD

The present invention relates to a novel6-(1fluoroethyl)-5-iodo-4-aminopyrimidine compound useful asagricultural and horticultural chemicals for controlling noxiousorganisms.

BACKGROUND ART

The 6-(1-fluoroethyl)-5-iodo-4-aminopyrimidine compound of the presentinvention is a novel compound and it has not been known that it hasagricultural and horticultural effects of controlling noxious organisms.

An object of the present invention is to provide a novel6-(1-fluoroethyl)-5-iodo-4-aminopyrimidine compound, a process forpreparing the same and agricultural and horticultural chemicals forcontrolling noxious organisms containing the same as an effectiveingredient.

DISCLOSURE OF THE INVENTION

The present inventors have studied to solve the above-mentionedproblems, and as a result, they have found that novel6-(1-fluoroethyl)-5-iodo-4-aminopyrimidine compounds have remarkableinsecticidal, acaricidal, nematocidal and fungicidal effects for anagricultural and horticultural use, whereby they have accomplished thepresent invention.

That is, the present invention is as shown below.

The first invention relates to a6-(1-fluoroethyl)-5iodo-4-aminopyrimidine compound represented by thefollowing formula (1):

-   -   wherein Ar represents a phenyl group, a naphthyl group, a        thienyl group, an indanyl group or a 1,4benzodioxan-6-yl group,        which is unsubstituted or substituted by 1 to 3 substituents        selected from the group consisting of a halogen atom, an alkyl        group having 1 to 4 carbon atoms, a haloalkyl group having 1 to        4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a        haloalkoxy group having 1 to 4 carbon atoms and a phenoxy group;        R represents a hydrogen atom or an alkyl group having 1 to 4        carbon atoms; *1 represents an asymmetric carbon atom; *2        represents an asymmetric carbon atom when R represents an alkyl        group having 1 to 4 carbon atoms.

The second invention relates to a process for preparing the6-(1-fluoroethyl)-5-iodo-4-aminopyrimidine compound represented by theabove-mentioned formula (1), which comprises reacting4-chloro-6-(1-fluoroethyl)-5-iodopyrimidine represented by the followingformula (2):

-   -   wherein *1 has the same meaning as defined above, with an amine        represented by the following formula (3):    -   wherein Ar, R and *2 have the same meanings as defined above.

The third invention relates to an agricultural and horticulturalchemicals for controlling noxious organisms containing the6-(1-fluoroethyl)-5-iodo-4-aminopyrimidine compound represented by theabove-mentioned formula (1) as an effective ingredient.

BEST MODE FOR CARRYING OUT THE INVENTION

In the following, the present invention will be explained in detail.

The respective substituents shown in the above-mentioned respectivecompounds are as mentioned below.

Ar is a phenyl group, a naphthyl group, a thienyl group, an indanylgroup or a 1,4-benzodioxan-6-yl group, which is unsubstituted orsubstituted by 1 to 3 substituents selected from the group consisting ofa halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkylgroup having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbonatoms, a haloalkoxy group having 1 to 4 carbon atoms and a phenoxygroup.

R is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

*1 is an asymmetric carbon atom.

*2 is an asymmetric carbon atom when R is an alkyl group having 1 to 4carbon atoms.

As the halogen atom which is a substituent for Ar, there may bementioned, for example, a chlorine atom, an iodine atom, a bromine atom,a fluorine atom, etc., and preferably a chlorine atom and a fluorineatom.

As the alkyl group having 1 to 4 carbon atoms which is a substituent forAr, there may be mentioned, for example, a straight or branched alkylgroup, and preferably a methyl group, an ethyl group, an isopropyl groupand a t-butyl group.

As the haloalkyl group having 1 to 4 carbon atoms which is a substituentfor Ar, there may be mentioned, for example, a difluoromethyl group, atrifluoromethyl group, 2,2,2-trifluoroethyl group, a 2-fluoroethylgroup, etc., preferably a trifluoromethyl group.

As the alkoxy group having 1 to 4 carbon atoms which is a substituentfor Ar, there may be mentioned, for example, a straight or branchedalkoxy group, preferably a methoxy group and an ethoxy group.

As the haloalkoxy group having 1 to 4 carbon atoms which is asubstituent for Ar, there may be mentioned, for example, adifluoromethoxy group, a trifluoromethoxy group, 2,2,2-trifluoroethoxygroup, a 2-trifluoroethoxy group, etc., and preferably a difluoromethoxygroup and a trifluoromethoxy group.

As the phenoxy group which is a substituent for Ar, there may bementioned, for example, a phenoxy group which may be substituted by theabove-mentioned halogen atom, the alkyl group having 1 to 4 carbonatoms, the haloalkyl group having 1 to 4 carbon atoms, the alkoxy grouphaving 1 to 4 carbon atoms or a haloalkoxy group having 1 to 4 carbonatoms, preferably an unsubstituted phenoxy group.

A number of these substituents is preferably 1 to 3.

As the alkyl group having 1 to 4 carbon atoms of R, there may bementioned, for example, a straight or branched alkyl group, andpreferably a methyl group, an ethyl group, an i-propyl group, a n-butylgroup and an i-butyl group.

The compound (1) of the present invention has an amino group so that anacid addition salt derived therefrom is also included in the presentinvention.

As an acid which forms an acid addition salt, there may be mentioned,for example, an inorganic acid such as hydrochloric acid, hydrobromicacid, nitric acid, sulfuric acid, phosphoric acid, etc.; a carboxylicacid such as formic acid, oxalic acid, fumaric acid, adipic acid,stearic acid, oleic acid, aconitic acid, etc.; a sulfonic acid such asmethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid,etc.; saccharine, etc.

Also, the compound (1) of the present invention contains an asymmetriccarbon atom represented by *1 and *2 so that the respective opticalisomers, racemic isomers, diastereomers or a mixture thereof derivedtherefrom are each included in the present invention.

Among the compounds (1) of the present invention, particularly preferredcompounds may include the following.

-   (1) A compound in which R is a hydrogen atom, and Ar is a phenyl    group substituted by an alkoxy group having 1 to 4 carbon atoms. For    example, there may be mentioned Compounds 5, 6, etc. shown in Table    1 mentioned below.-   (2) A compound in which R is a hydrogen atom, and Ar is a phenyl    group substituted by an alkyl group having 1 to 4 carbon atoms. For    example, there may be mentioned Compounds 1, 2, 11, etc. shown in    Table 1 mentioned below.-   (3) A compound in which R is a hydrogen atom, and Ar is a phenyl    group substituted by a phenoxy group. For example, there may be    mentioned Compound 12, etc. shown in Table 1 mentioned below.-   (4) A compound in which R is an alkyl group having 1 to 4 carbon    atoms, and Ar is an unsubstituted phenyl group. For example, there    may be mentioned Compounds 13 to 18, etc. shown in Table 1 mentioned    below.-   (5) A compound in which R is an alkyl group having 1 to 4 carbon    atoms, and Ar is a phenyl group substituted by a haloalkoxy group    having 1 to 4 carbon atoms and a halogen atom. For example, there    may be mentioned Compound 22, etc. shown in Table 1 mentioned below.-   (6) A compound in which R is an alkyl group having 1 to 4 carbon    atoms, and Ar is a phenyl group substituted by a haloalkoxy group    having 1 to 4 carbon atoms. For example, there may be mentioned    Compounds 20, 21, 23, etc. shown in Table 1 mentioned below.-   (7) A compound in which R is an alkyl group having 1 to 4 carbon    atoms, and Ar is a phenyl group substituted by a halogen atom. For    example, there may be mentioned Compounds 24, 25, etc. shown in    Table 1 mentioned below.-   (8) A compound in which R is an alkyl group having 1 to 4 carbon    atoms, and Ar is a phenyl group substituted by an alkyl group having    1 to 4 carbon atoms. For example, there may be mentioned Compounds    27, 28, etc. shown in Table 1 mentioned below.-   (9) A compound in which R is an alkyl group having 1 to 4 carbon    atoms, and Ar is an unsubstituted indanyl group. For example, there    may be mentioned Compounds 36, 37, etc. shown in Table 1 mentioned    below.-   (10) A compound in which R is an alkyl group having 1 to 4 carbon    atoms, and Ar is an unsubstituted 1,4-benzodioxan-6yl group. For    example, there may be mentioned Compound 39, etc. shown in Table 1    mentioned below.-   (11) A compound in which R is a hydrogen atom, and Ar is a phenyl    group substituted by a halogen atom. For example, there may be    mentioned Compounds 3, 7, 8, etc. shown in Table 1 mentioned below.-   (12) A compound in which R is a hydrogen atom, and Ar is a phenyl    group substituted by a haloalkyl group having 1 to 4 carbon atoms.    For example, there may be mentioned Compound 4, etc. shown in Table    1 mentioned below.-   (13) A compound in which R is an alkyl group having 1 to 4 carbon    atoms, and Ar is an unsubstituted naphthyl group. For example, there    may be mentioned Compound 29, etc. shown in Table 1 mentioned below.-   (14) A compound in which R is an alkyl group having 1 to 4 carbon    atoms, and Ar is an unsubstituted thienyl group. For example, there    may be mentioned Compound 33, etc. shown in Table 1 mentioned below.

A synthetic method of the above-mentioned compound (1) according to thepresent invention is described in detail.

Synthetic Method

Compound (1) is synthesized by reacting Compound (2) with Compound (3)in a solvent, in the presence of a base.

As a kind of the solvent, it is not particularly limited so long as itdoes not directly participate in the present reaction, and there may bementioned, for example, a chlorinated or not chlorinated aromatic,aliphatic or alicyclic hydrocarbon such as benzene, toluene, xylene,methylnaphthalene, petroleum ether, ligroin, hexane, chlorobenzene,dichlorobenzene, chloroform, dichloroethane, trichloroethylene, etc.; anether such as tetrahydrofuran, dioxane, diethyl ether, etc.; a nitrilesuch as aceto-nitrile, propionitrile, etc.; a ketone such as acetone,methyl ethyl ketone, etc.; an aprotic polar solvent such asN,N-dimethylformamide, dimethylsulfoxide, sulforane,N,N-dimethylimidazolidinone, N-methylpyrrolidone, etc.; and a mixture ofthe above-mentioned solvents.

An amount of the solvent to be used is preferably such that the contentof Compound (2) becomes 5 to 80% by weight; and more preferably 10 to70% by weight.

A kind of the base is not specifically limited, and an organic base andan inorganic base are mentioned. There may be mentioned, for example, atertiary amine such as triethylamine, an organic base such as DBU, aninorganic base such as a hydride, hydroxide, carbonate, hydrogencarbonate of an alkali metal or an alkaline earth metal; and preferablyan organic base such as triethylamine.

An amount of the base to be used is preferably 1 to 5-fold mol, morepreferably 1.2 to 2.0-fold mol based on the amount of Compound (2).

A reaction temperature is not specifically limited, and it is preferablywithin the temperature range from a room temperature to a boiling pointor less of the solvent to be used, particularly preferably 60 to 110° C.

A reaction time may vary depending on the above-mentioned concentrationand temperature, and generally 0.5 to 8 hours.

An amount of the starting compound to be used is preferably 1.0 to5-fold mol of Compound (3) based on the amount of Compound (2), and morepreferably 1 to 1.1-fold mol.

Compound (2) to be used in the present invention can be prepared by themethod shown in the following scheme according to the description ofJapanese Patent Application No. 2000-384776.

-   -   wherein *1 has the same meaning as defined above.

Compound (4) can be prepared, for example, by the method according toJapanese Provisional Patent Application No. 171834/1999.

Compound (3) may be a commercially available product or may be preparedby the method shown in the following scheme.

-   -   wherein Ar, R and *2 have the same meanings as defined above.

The desired Compound (1) prepared as mentioned above may be subjected tousual post-treatment such as extraction, concentration, filtration, etc.after completion of the reaction, and, if necessary, may be subjected topurification by the known methods such as recrystallization, variouskinds of chromatographies, etc.

Controlling Effects

As the agricultural and horticultural noxious organisms on which acontrolling effect by the compound (1) of the present invention can beobserved, there may be mentioned agricultural and horticultural noxiousinsects [e.g. Hemiptera (planthoppers, leafhoppers, aphides, whiteflies,etc.), Lepidoptera (cabbage armyworms, diamond-back moth, leaf rollermoths, pyralid moths, codling moths, cabbage butterfly, etc.),Coleoptera Tenebrionid beetles, leafbeetles, weevils, scarabs, etc.),Acarina (citrus red mite, two-spotted spider mite, etc. of Tetranychidaefamily, pink citrus rust mite of Eriophyidae family, etc.)], nematodes(e.g. root knot nematodes, cystcid nematodes, root lesion nematode ,white-tip nematodes, pine wood nematodes), bulb mite in soil,hygienically noxious insects (e.g. flies, mosquitoes, cockroaches,etc.), noxious insects of stored grains (e.g. rust-red flour beetles,bean weevils, etc.), wood insects (e.g. termite such as Formosansubterranean termite, Reticulitermes separatus and Cryptotermesdomesticus; powderpost beetles, drugstore beetles, carpenter moths,long-horned beetle, bark beetles, etc.) and also agricultural andhorticultural diseases (e.g. monilia furcticola, wheat brown rust,barley powdery mildew, cucumber downy mildew, rice blast (pyriculariaozyzea), tomato late blight, etc.).

Chemical for Controlling Noxious Organisms

The agricultural and horticultural chemical for controlling noxiousorganisms of the present invention has particularly remarkable ininsecticidal, acaricidal and nematocidal effects, and contains one ormore kinds of Compound (1) as an effective ingredient.

Compound (1) may be used singly, however, it is generally preferred touse the same by formulating a carrier, surfactant, dispersant,auxiliary, etc. (for example, it is prepared as a composition such asdust powder, an emulsifiable concentrate, a fine granule, a granule, awettable powder, an oily suspension, an aerosol, etc.) according to theconventionally known method.

As the carrier, there may be mentioned, for example, a solid carriersuch as talc, bentonite, clay, kaolin, diatomaceous earth, white carbon,vermiculite, calcium hydroxide, siliceous sand, ammonium sulfate, urea,etc., a liquid carrier such as hydrocarbon (kerosine, mineral oil,etc.), aromatic hydrocarbon, (benzene, toluene, xylene, etc.),chlorinated hydrocarbon (chloroform, carbon tetrachloride, etc.), ethers(dioxane, tetrahydrofuran, etc.), ketones (acetone, cyclohexanone,isophorone, etc.), esters (ethyl acetate, ethyleneglycol acetate,dibutyl maleate, etc.), alcohols (methanol, n-hexanol, ethylene glycol,etc.), aprotic polar solvent (dimethylformamide, dimethylsulfoxide,etc.), water, etc.; a gas carrier such as air, nitrogen, a carbondioxide gas, fleone, etc. (in this case, mixture spreading can becarried out), and the like.

As the surfactant and dispersant which can be used for improvingattachment of the present chemical to and absorption thereof in animalsand plants, and improving characteristics such as dispersion,emulsification and spreading of the chemical, there may be mentioned,for example, alcohol sulfates, alkylsulfonate, lignosulfonate andpolyoxyethylene glycol ether. As a surfactant, there may be usedcommercially available products, for example, Neopelex powder (tradename, produced by Kao K. K.), Demol (trade name, produced by Kao K. K.),Toxanone (trade name, produced by Sanyo Chemical Industries, Ltd.) andthe like. Further, for improving properties of its formulation, forexample, carboxymethyl cellulose, polyethylene glycol and gum arabic canbe used as an auxiliary.

In preparation of the present chemical, the above-mentioned carrier,surfactant, dispersant and auxiliary can be used singly or in a suitablecombination, respectively, depending on the respective purposes.

When the compound (1) of the present invention is made intoformulations, the concentration of the active ingredient is generally 1to 50% by weight in an emulsifyable concentrate, generally 0.3 to 25% byweight in a dustable powder, generally 1 to 90% by weight in a wettablepowder, generally 0.5 to 5% by weight in a granule, generally 0.5 to 5%by weight in an oily suspension, and generally 0.1 to 5% by weight in anaerosol.

These formulations can be provided for various uses by diluting them toa suitable concentration and spraying them to stems and leaves ofplants, soil and paddy field surface, or by applying them directlythereto, depending on the purposes.

EXAMPLE

In the following, the present invention will be explained specificallyby referring to Reference examples and Examples. Incidentally, thesewill not limit the scope of the present invention.

Reference Example 1 (Synthetic Method of Compound (5))

Synthesis of 6-(1-fluoroethyl)-4-pyrimidone

In methanol (1000 ml) was dissolved methyl 4-fluoro3-oxopentanoate (93.3g), and a 28% sodium methylate/methanol solution (365 g) and formamidineacetate (98.4 g) were successively added to the solution, and theresulting mixture was refluxed at 40° C. for 12 hours.

After completion of the reaction, the mixture was cooled to 10° C. orlower, and a mixture of conc. sulfuric acid (95.1 g) and water (85 g)was added to the above mixture. Then, the mixture was stirred at 50° C.for 30 minutes, insoluble materials were removed by filtration, and thefiltrate was concentrated under reduced pressure. The resulting residuewas recrystallized from isopropanol to obtain 58 g of the desiredcompound as colorless crystal.

m.p. 170.0 to 171.5° C.

Reference Example 2 (Synthetic Method of Compound (6))

Synthesis of 6-(1-fluoroethyl)-5-iodo-4-pyrimidone

To an acetic acid (150 ml) solution of 6-(1fluoroethyl)-4-pyrimidone(56.8 g) was added dropwise under room temperature and stirring anacetic acid solution of iodine monochloride prepared by adding iodine(50.8 g) to acetic acid (500 ml) and blowing chlorine (15 g) thereintounder room temperature and stirring, and the resulting mixture wasstirred for 6 hours.

After completion of the reaction, the acetic acid was removed underreduced pressure, water (300 ml) was added to the residue to dissolvethe material, and pH of the mixture was adjusted to 5 with 2N sodiumhydroxide and an aqueous saturated sodium hydrogen carbonate solution.The precipitated crystals were collected by filtration, washed withwater and dried to obtain 85 g of the desired product as pale ocherouscrystal.

Moreover, the crystal was purified by recrystallization from ethylacetate-hexane to obtain 76.0 g of the desired product as colorlessneedle-like crystal.

m.p. 195 to 196° C.

Reference Example 3 (Synthetic Method of Compound (2))

Synthesis of 4-chloro-6-(1-fluoroethyl)-5-iodopyrimidine

To ethyl acetate (180 ml) was added6-(1-fluoroethyl)-5-iodo-4-pyrimidone (53.6 g), N,N-dimethylformamide(1.5 g) was added to the mixture and the resulting mixture was stirredat 70° C. while heating. Subsequently, thionyl chloride (28.6 g) wasadded dropwise to the mixture and stirred for 3 hours to complete thereaction.

After cooling the reaction mixture, the mixture was poured into ice-coldwater, and pH of the mixture was adjusted to 4 with 2N sodium hydroxide.The ethyl acetate layer was collected by separation, washed with water,and then, dried over anhydrous sodium sulfate. Subsequently, underreduced pressure, the solvent was removed by distillation, and theobtained residue was purified by distillation under reduced pressure toobtain 54.6 g of the desired compound as a pale yellowish liquid.

b.p. 116 to 118° C./4 mmHg

Example 1 (Synthetic Method of Compound (1))

(1) Synthesis of4-(4-t-butylbenzylamino)-6-(1-fluoroethyl)-5-iodopyrimidine (Compound 1)

In 20 ml of toluene were dissolved 4-t-butylbenzyl-amine (0.8 g) andtriethylamine (0.6 g), and 4-chloro-6-(1-fluoroethyl)-5-iodopyrimidine(1.5 g) was added to the solution and the resulting mixture was stirredat about 80° C. for 3 hours.

After completion of the reaction, triethylamine hydrochloride wasremoved by filtration, the solvent was removed under reduced pressure,and the obtained residue was purified by silica gel columnchromatography (Wako gel C-200, eluent; n-hexane/ethyl acetate=3/1) toobtain 1.5 g of the objective product as colorless small plate-shapedcrystal.

m.p. 114 to 115° C.; ¹H-NMR (CDCl₃, δ ppm); 1.32 (9H, s), 1.61 to 1.71(3H, d-d), 4.68 to 4.70 (2H, d), 3.74 to 3.81 (2H, q), 5.70 to 5.92 (1H,d-q), 5.76 (1H, b), 7.26 to 7.41 (4H, m), 8.50 (1H, s).

(2) Synthesis of6-(1-fluoroethyl)-5-iodo-4-(α-methyl-benzylamino)pyrimidine (Compound13)

In 40 ml of toluene were dissolved α-methylbenzyl-amine (1.2 g) andtriethylamine (1.2 g), and 4-chloro-6-(1-fluoroethyl)-5-iodopyrimidine(2.9 g) was added to the solution and the resulting mixture was stirredat about 80° C. for 3 hours.

After completion of the reaction, triethylamine hydrochloride wasremoved by filtration, the solvent was removed under reduced pressure,and the obtained residue was purified by silica gel columnchromatography (Wako gel C-200, eluent; n-hexane/ethyl acetate=3/1) toobtain 2.9 g of the desired product as a pale orange viscous liquid.

¹H-NMR (CDCl₃, δ ppm); 1.57 to 1.69 (6H, m), 4.68 to 4.70 (2H, d), 5.24to 5.92 (1H, d-q), 5.83 (1H, b), 7.24 to 7.37 (5H, m), 8.43 (1H, s).

(3) Synthesis of other Compound (1) in Table 1

According to the methods described in the above-mentioned (1) and (2),other compounds (1) in Table 1 were synthesized.

The compounds (1) synthesized as mentioned above and their physicalproperties are shown in Table 1.

*1 is all racemic mixtures (R,S).

TABLE 1 (1)

Com- Physical pound Ar R *2 property 1

H R, S m.p.114˜ 115° C. 2

H R, S m.p.80˜ 81° C. 3

H R, S m.p.105˜ 106° C. 4

H R, S m.p.112˜ 113° C. 5

H R, S n_(D) ^(21.9) 1.6089 6

H R, S m.p.82˜ 63° C. 7

H R, S m.p.72˜ 73° C. 8

H R, S m.p.69˜ 71° C. 9

H R, S 10

H R, S 11

H R, S m.p.62˜ 63° C. 12

H R, S n_(D) ^(18.8) 1.6145 13

CH₃ R, S n_(D) ^(22.9) 1.6053 14

CH₃ S n_(D) ^(22.3) 1.6061 15

CH₃ R n_(D) ^(23.2) 1.6065 16

C₂H₅ R, S n_(D) ^(23.1) 1.5993 17

C₄H₉-n R, S n_(D) ^(18.9) 1.5827 18

C₄H₉-i R, S n_(D) ^(23.7) 1.5831 19

CH₃ R, S 20

C₂H₅ R, S n_(D) ^(22.5) 1.5645 21

C₂H₅ R, S unable to measure 22

CH₃ R, S n_(D) ^(23.4) 1.5755 23

CH₃ R, S n_(D) ^(22.5) 1.5675 24

C₂H₅ R, S n_(D) ^(23.1) 1.6002 25

CH₃ R, S n_(D) ^(23.7) 1.6006 26

CH₃ R, S n_(D) ^(23.6) 1.5936 27

CH₃ R, S n_(D) ^(23.7) 1.5842 28

CH₃ R, S n_(D) ^(23.5) 1.5837 29

CH₃ R, S m.p.110˜ 112° C. 30

CH₃ R, S 31

C₂H₅ R, S 32

CH₃ R, S 33

CH₃ R, S n_(D) ^(23.3) 1.6105 34

CH₃ R, S 35

CH₃ R, S 36

CH₃ R, S n_(D) ^(19.5) 1.5923 37

C₂H₅ R, S n_(D) ^(19.3) 1.5856 38

CH₃ R, S 39

CH₃ R, S n_(D) ^(19.1) 1.5835 40

CH₃ R, S

Example 2 (Preparation of Formulations)

(1) Preparation of Granule

Five parts by weight of Compound (1) were uniformly mixed with 35 partsby weight of bentonite, 57 parts by weight of talc, 1 part by weight ofNeopelex powder (trade name, produced by Kao K. K.) and 2 parts byweight of sodium lignosulfonate, then the mixture was kneaded withaddition of a small amount of water, followed by granulation and drying,to obtain a granule.

(2) Preparation of Wettable Powder

Ten parts by weight of Compound (1) were uniformly mixed with 70 partsby weight of kaolin, 18 parts by weight of white carbon, 1.5 parts byweight of Neopelex powder (trade name, produced by Kao K. K.) and 0.5part by weight of Demol (trade name, produced by Kao K. K.), then themixture was pulverized to obtain a wettable powder.

(3) Preparation of Emulsifiable Concentrate

Twenty parts by weight of Compound (1) were uniformly mixed with 70parts by weight of xylene by adding 10 parts by weight of Toxanone(trade name, produced by Sanyo Chemical Industries, Ltd.), and mixedtherein uniformly to obtain an emulsifiable concentrate.

(4) Preparation of Dustable Powder

Five parts by weight of Compound (1) were uniformly mixed with 50 partsby weight of talc and 45 parts by weight of kaolin to obtain dustablepowder.

Example 3 (Tests of Effects)

(1) Test of Effect on Green Caterpillar (Common Cabbage Worm)

The respective wettable powders of Compounds (1) shown in Table 1prepared as in Example 2 were diluted to 1000 ppm with water containinga surfactant (0.01%), and in these respective chemical solutions,cabbage leaves (5×5 cm) were dipped for 30 seconds, and each leaf wasput into the respective plastic cups and air-dried.

Subsequently, 10 green caterpillars (3rd instar larvae) were placed inthe respective cups, which were sealed by lids, and they were left tostand in a thermostat chamber at 25° C. After 2 days, insecticidal ratewas determined by counting living and dead insects in the respectivecups.

As a result, Compounds 1 to 8, 11 to 18, 20 to 29, 33, 36, 37, 39 showedthe insecticidal effect of 80% or more.

(2) Test of Effect on Green Peach Aphid

The respective wettable powders of Compounds (1) shown in Table 1prepared as in Example 2 were diluted to 100 ppm with water containing asurfactant (0.01%), and in these respective chemical solutions, cabbageleaves (5×5 cm) were dipped for 30 seconds, and each leaf was put intothe respective plastic cups and air-dried.

Subsequently, 10 green peach aphids (apterous female adults) were placedin the respective cups, which were sealed by lids, and they were left tostand in a thermostat chamber at 25° C. After 3 days, insecticidal ratewas determined by counting living and dead apterous female adults andlarvaes in the respective cups.

As a result, Compounds 6, 11 to 14, 16, 22 to 25, 27, 28, 37 and 39showed the insecticidal effect of 80% or more.

(3) Antibacterial Test

Acetone solutions of Compounds (1) shown in Table 1 were migrated into aPDA (potato dextrose agar) medium with a final concentration of 40 ppmto prepare plate culture media.

Respective colonies of monilia furcticola and pyricularia oryzea eachpreviously grown in PDA plate culture media were cut with 1 mm square bya scalpel and inoculated to plate culture media containing chemicals.

They were cultured at 25° C. under dark place for 3 days, and thediameter of the colony was compared to those grown in the area to whichno chemical was added, and a colony growth-inhibiting ratio (%) wascalculated by the following equation. $\begin{matrix}{{Colony}\quad{growth}} \\{{inhibiting}\quad{ratio}\quad(\%)}\end{matrix} = {\left( {1 - \frac{\begin{matrix}{{Diameter}\quad({mm})\quad{of}\quad{colony}} \\{{grown}\quad{in}\quad{chemical}\quad{treated}\quad{area}}\end{matrix}}{\begin{matrix}{{Diameter}\quad({mm})\quad{of}\quad{colony}\quad{grown}} \\{{in}\quad{chemical}\quad{non}\text{-}{treated}\quad{area}}\end{matrix}}} \right) \times 100}$

Judgment of the effects was carried out with 6 ranks from 5 to 0 inwhich a colony growth-inhibiting ratio of 95 to 100% was rated 5, 85 to95% was 4, 85 to 70% was 3, 45 to 70% was 2, 10 to 45% was 1, and 10 to0% was 0.

As a result, Compounds 2 to 8, 11 to 18, 20 to 29, 33, 36, 37 and 39showed effects of 4 or more against monilia furcticola, and Compounds 1to 8, 11 to 18, 20 to 29, 33, 37 and 39 showed effects of 4 or moreagainst pyricularia oryzea.

Industrial Applicability

The novel 6-(1-fluoroethyl)-5-iodo-4-aminopyrimidine compound of thepresent invention has excellent effects of controlling noxious organismsfor an agricultural and horticultural use.

1. A 6-(1-fluoroethyl)-5 iodo-4-aminopyrimidine compound represented bythe following formula (1):

wherein Ar represents a phenyl group, a naphthyl group, a thienyl group,an indanyl group or a 1,4-benzodioxan-6-yl group, which is unsubstitutedor substituted by 1 to 3 substituents selected from the group consistingof a halogen atom, an alkyl group having 1 to 4 carbon atoms, ahaloalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to4 carbon atoms, a haloalkoxy group having 1 to 4 carbon atoms and aphenoxy group; R represents a hydrogen atom or an alkyl group having 1to 4 carbon atoms; *1 represents an asymmetric carbon atom *2 representsan asymmetric carbon atom when R represents an alkyl group having 1 to 4carbon atoms.
 2. The 6-(1-fluoroethyl)-5-iodo-4-aminopyrimidine compoundaccording to claim 1, wherein Ar in the above mentioned formula (1) is aphenyl group substituted by 1 to 3 substituents selected from the groupconsisting of a halogen atom, an alkyl group having 1 to 4 carbon atoms,a halo-alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1to 4 carbon atoms, a haloalkoxy group having 1 to 4 carbon atoms and aphenoxy group, or an unsubstituted phenyl group.
 3. The6-(1-fluoroethyl)-5-iodo-4-aminopyrimidine compound according to claim1, wherein the substituent for Ar is selected from the group consistingof a chlorine atom, a fluorine atom, a methyl group, an ethyl group, anisopropyl group, a t-butyl group, a trifluoromethyl group, a methoxygroup, an ethoxy group, a difluoromethoxy group, a trifluoromethoxygroup and an unsubstituted phenoxy group.
 4. The6-(1-fluoroethyl)-1)-5-iodo-4-aminopyrimidine compound according toclaim 1, wherein R is a hydrogen atom, a methyl group, an ethyl group,an I-propyl group, a n-butyl group or an I-butyl group.
 5. The6-(1-fluoroethyl)-5-iodo-4-aminopyrimidine compound according to claim1, wherein Ar represents an phenyl group substituted with an alkyl grouphaving 1 to 4 carbon atoms and R is a hydrogen atom or an alkyl grouphaving 1 to 4 carbon atoms.
 6. A process for preparing the6-(1-fluoroethyl)-5-iodo-4-aminopyrimidine compound represented by theformula (1) according to claim 1, which comprises reacting4-chloro-6-(1- fluoroethyl)-5-iodopyrimidine represented by thefollowing formula (2):

wherein *1 has the same meaning as defined in claim 1, with an aminerepresented by the following formula (3):

wherein Ar, R and *2 have the same meanings as define in claim
 1. 7. Anagricultural or horticultural composition for controlling noxiousorganisms comprising the 6-(1-fluoroethyl)-5 -iodo-4 -aminopyrimidinecompound represented by the formula (1) according to claim 1 as aneffective ingredient, and a carrier.